I'm riding (not successfully) the CWB Benz - 4'8". I can ride the wake holding the rope easily, but it's impossible for me to stay on top the water and find the sweet spot in the wake. Super frustrating.

That board design is way to small. Red Woody or one of the big rider Phase Five boards is the way to go. Spend the money and do some riding. The sensation you get the first time you go without the rope is worth the price of the board on the first ride.

The only beef I have with the custom boards is they tend to be fragile. The Red Woody is not as tough as your CWB but it will be tougher than a hand laid fiberglass board.

I am 250 lbs, and I surf 3 times a week.
I have taught over 500 people successfully to wakesurf. 100% have dropped the rope.http://www.surfthirty.com/ - check out the video tab for lots of first timers...
You do NOT need a custom board yet, first get up on a factory board, and get some fun...
Here are some widely available boards that WILL work for you:
- Liquid Force Noserider - http://bit.ly/1e3Kvj4
You need the 5'6" board - $550 list, $399 or better online
- Hyperlite Landlock 5'11" - http://bit.ly/15Srvlm -
$335 list, $239 or better online

I'm riding (not successfully) the CWB Benz - 4'8". I can ride the wake holding the rope easily, but it's impossible for me to stay on top the water and find the sweet spot in the wake. Super frustrating.

My SIL is 6'3" ~275 and rides the CWB Ride. Its our starter/beginner board and all have been able to ride it.

5'8" and 6'3" ..... my ocean board is 5'10". That seems a little longer than needed. Nothing wrong with going custom. Go 2.5" rocker on a 4'8" board that's thick for weight and you will have no trouble surfing. And have no need to upgrade. Spend about the same price too.

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__________________

When I was a child, I used to talk as a child, think as a child, reason as a child; when I became a man, I put aside childish things.
1 Corinthians Chapter 13 - 11

I am 250 lbs, and I surf 3 times a week.
I have taught over 500 people successfully to wakesurf. 100% have dropped the rope.http://www.surfthirty.com/ - check out the video tab for lots of first timers...
You do NOT need a custom board yet, first get up on a factory board, and get some fun...
Here are some widely available boards that WILL work for you:
- Liquid Force Noserider - http://bit.ly/1e3Kvj4
You need the 5'6" board - $550 list, $399 or better online
- Hyperlite Landlock 5'11" - http://bit.ly/15Srvlm -
$335 list, $239 or better online

x2 on a bigger board, x2 on buying a used production board until you improve, THEN buying a custom board tailored to your style and abilities. As someone said above, the highend/custom boards are very fragile, and not something you want to deal with while learning.

Couple ideas: We keep a 5'6" Grindwater Mauka on the boat for beginners (and ballast boys wanting a break from the beer), and previously had a similar Hyperlite Broadcast that was bulletproof. FWIW, we bought the Grindwater NEW for $230 from local shop (closeout model).